The Founder’s Plunge
I took the plunge into entrepreneurship (and you should too)
Taking the plunge into entrepreneurship is exhilarating and terrifying. It’s like waking up each morning and diving into an icy lake of unknown depth. Uncertainty looms large.
My baseline anxiety is probably higher than it used to be. I know it’s not a life or death situation, but my body can hardly tell the difference.
At times, I question whether I made the right decision. It’s difficult to justify the opportunity cost of a comfortable salary and cushy job.
I wonder, what are the odds that my startup succeeds?
Oh…
Seeing data like this is a bit scary.
It feels irrational — almost delusional — to bet against the 90% majority.
While I’m confident that I can work harder and smarter than 9 out of 10 people, I can’t control all the variables, and i’m not hardheaded enough to presume I can always beat the odds.
Starting a business is often one of the most important decisions we make in our lives.
I’ve had the urge to take the plunge for as long as I can remember, and for the past few years, I’ve developed an idea compelling enough to leave my stable life behind and explore it further.
I wonder, how often do people try to turn their idea into a business?
So, 92% of people that had a dream to start a business never even tried to make it a reality!
Seeing data like this gives me the courage to take my chances.
One thing is for certain, I am not going to be in the majority that never tried.
Risky Business
When is the best time to take the plunge and found a company?
The common advice is to wait until you’ve de-risked the decision by keeping your day job until the side-gig has sufficient revenue and growth. This way you never lose your income, and the transition to entrepreneurship is organic and smooth.
Unfortunately, this advice didn’t work for me.
My full-time job was just that: full-time. I chose a career that did not include the luxury of free time.
Sure, I worked most weekends on my passion project, but a full-day of work every day, Monday thru Friday, left me exhausted and lacking the energy to work much during the week.
This means at best, I could put in 20 hours of work on my passion project.
The problem is, during the day I competed with people more passionate about my day job than I was, and at night I competed with people who poured an entire week’s worth of time and energy into their passion project.
My plan B was someone else’s plan A.
Thanks to this predicament, I was doomed to never quite de-risk the decision to take the plunge. My time and energy was split such that I would not master either pursuit in any realistic time frame. For years, I existed in this limbo.
Then one day, I reframed the risk equation.
It was no longer about cash flow and probability of success. The risk of losing income was a rounding error compared to the risk of losing another year of my life stuck in limbo.
The time to found a company was not when I had sufficient revenue and a clear path to success.
The time was now.
Fuck You Money vs Fuck This Money
What does it actually take to leave your job and turn a dream into a business?
I can say from experience, it takes more than just courage and timing. It also takes a lot of money.
Fortunately, you don’t need “fuck you money” to start your own business. For those unfamiliar, fuck you money describes the amount of wealth required to do what you want, when you want, and not care what anyone says or thinks about it. This number is often measured in nine or ten figures, and the people in this tier of wealth might found a new business as casually as the rest of us buy new socks.
Instead, quitting your job and setting out to build a business takes what I’ve dubbed “fuck this money”.
This is the amount of money it takes for you to confidently proclaim, “fuck this, I’m out” to your current situation and walk away.
It’s roughly the amount of money you need to support yourself while bootstrapping a new endeavor for at least a year.
You need enough money saved up to pay for food, shelter, and insurance for more than a year on top of any business related expenses. I can promise you, the government is not going to help much and it’s almost certainly going to take longer than you think, so make sure you have plenty of buffer.
At the start of 2023, I had saved up enough money to buy a house, but due to the economic climate, it seemed the wrong time to invest in real estate, so instead, I decided to invest in founding my business.
It was painful to see my projected income for 2023 (or lack thereof), but I knew I had enough cash in the bank to support myself for at least a year, and that was all I needed.
I had fuck-this money and I wasn’t afraid to use it.
Founding a startup means you probably won’t have as much income as you used to for a while, but the good news is, you can control the other side of the balance sheet. You can choose what you’re willing to live without, and if you’re willing to make sacrifices, you can extend your runway much longer than you think.
Choose Your Sacrifices
I didn’t choose where or when I was born. I didn’t choose my family or the first language I spoke.
However, I am blessed with the freedom to choose my sacrifices.
Taking the plunge into entrepreneurship meant making sacrifices in other important areas of my life. I had to let go of some amenities and even some meaningful relationships. I also had to say no to many other career opportunities and invitations for fun activities.
Some of the choices weren’t so hard, like sacrificing watching sports on Sundays to focus on work, but other choices were challenging, like not attending friend celebrations or visiting my family less often.
When we choose one path, we also choose NOT to follow another.
I’ve found it helpful to frame decisions in this way. It forces me to focus my limited resources and explicitly say no to other enticing options.
I am still learning how to say no and choose my sacrifices, but here are some things that have worked for me so far:
- Work with friends
Finding the right people to work with can make it far easier to make the requisite sacrifices. Founding a company with a couple of my closest friends makes working on a risky startup much more fun and it also makes it far easier to say no to alternatives. Find friends that are willing to do hard things with you (thank you, Jordan & Lucas). - Live somewhere inexpensive
This seems obvious but it took a while for me to actually make a move to live somewhere less expensive. For me this meant recently moving overseas to a place where I could stretch a dollar much further, but in the past, it also meant living with a parent (thank you, Dad). - Optimize your leisure
Try to simplify your leisure activities to those that give you the greatest energy and mood benefit for the time and money invested. For me, this was weekly soccer games, pickle ball, and game nights. - Don’t watch sports
I’ve saved much time and money by not getting too invested in watching sports; this means no betting, no fantasy sports, and watching live matches only on occasion. It also helps if your favorite team is garbage (thank you, Russell Wilson). - Cancel subscriptions
I canceled almost all content subscriptions — and payed to remove ads on my most-used streaming service, YouTube. Removing ads on videos has cumulatively saved me hours of wasted time, and ultimately, limiting myself to a single subscription has saved money too. And thankfully, my friends and family let me borrow their streaming accounts if there’s content I really want to see (thank you, Chris & many others). - Exercise efficiently
One lasting positive change from COVID has been learning how to exercise at home including practicing my own yoga flow, HIIT workouts, and TRX. With TRX, I never have an excuse to miss a workout. It’s inexpensive, quick to execute wherever you are, and the workout is as challenging as you make it. TRX and HIIT workouts have allowed me to actually cancel my gym membership and only go to the gym on occasion with my friend’s guest pass for a year (thank you, Lucas & Sofia). - Eat in
I love eating out at restaurants, but I had to sacrifice this habit to reduce my expenses and save time. Figure out the handful of meals that you enjoy, acquire them at low cost, and customize them to your taste and nutritional needs. For me, this meant purchasing a handful of fresh and frozen ingredients from Trader Joe’s and cycling thru my favorite meals, expending little energy and time determining what to make and how to prepare it. - Live near loved ones
Living close to friends has made it easier to maintain a healthy social life, but it can also make it more difficult to say no to invites. One of the best parts of living in close proximity to loved ones is the ability to spend quality time together without spending too much money, but at times, it also made my FOMO more acute.
Come on in, the Water is Freezing!
There is nothing more unpleasant to me than an icy cold plunge , which is exactly why one of my goals this year is to make ice baths a weekly habit. Doing challenging things is the surest way to grow, but growth is uncomfortable.
Starting a new business meant sacrificing a more stable life for an uncertain future with an uncertain payoff — pushing far past my comfort zone and standing on the precipice of the unknown.
If you read this essay and you decide the founder life is not for you, then by all means, step back from the edge and enjoy a warm, cozy career. You would be wise to listen to the startup success data.
But if you have the urge like I did, compelled to pursue a dream, it would be a shame to be in the majority of people that lived their whole life and never tried to turn their idea into a reality.
If you do decide to take the plunge, I’ll be right there with you. Besides, it’s really not so bad once you’re in.
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Shoutout to my co-founders, Jordan and Lucas, who also took the plunge and continue to inspire me to keep building and growing.
Photos are always by me. Sketches are always by me. Images are generated in Midjourney and edited by me.
